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Title:Polyandrocarpidines: Antimicrobial and Cytotoxic Compounds From the Marine Tunicate Polyandrocarpa Sp
Author(s):Cheng, Michael Tung-Hai
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract:The marine tunicate Polyandrocarpa sp. contains anti-microbial and cytotoxic metabolites, polyandrocarpidines, whose structures include a polymethylenediamine chain; one nitrogen is acylated with a twelve-carbon fatty acid which contains a cyclopropene ring in conjugation with a diene system, the other nitrogen is part of a primary guanidine function. It was advantageous to convert the guanidine to the dimethylpyrimidyl moiety by condensing with 2,4-pentanedione in the presence of sodium bicarbonate, because the dimethylpyrimidyl derivatives can be gas chromatographed, and the dimethylpyrimidyl moiety institutes very characteristic mass spectrometric fragmentations for the rest of the molecule.
Attempts to synthesize polyandrocarpidines were unsuccessful; however, hexahydropolyandrocarpidines were synthesized. Therefore, various analogs of hexahydropolyandrocarpidine were synthesized to study the structure-activity relationship against Bacillus subtilis. It was determined that the compound with five methylene groups between the two nitrogens has the highest activity, that the cyclopropane ring is not required for activity but its presence enhances the antimicrobial activity, and that the chain length of the acyl part is important to the activity.
Issue Date:1980
Description:170 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1980.
Other Identifier(s):(UMI)AAI8108462
Date Available in IDEALS:2014-12-13
Date Deposited:1980

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